Water → HCID 19911108, compound

HRID 1494286Notes

Reaction equation

HRID 1494286 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[OH-].[K+].[CH2:14]([OH:17])[CH2:15]Br.O>CN(C)C=O>[N+:9]([C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][C:2]=1[Cl:1])[O:8][CH:14]([OH:17])[CH3:15])([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 108982-Bromoethanol3×HCID 14797Potassium Hydroxide3×HCID 691274-Chloro-3-nitrophenol

Product 1

HCID 19911108HCID 19911108, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

2.5 mols (434 g) of 4-chloro-3-nitrophenol are dissolved in 1,300 ml of dimethylformamide heated to 70° C. beforehand. 3 mols of powdered potassium hydroxide (210 g of 80% pure potassium hydroxide) are added to this solution, and 3 mols (534 g) of glycol bromohydrin are then introduced in the course of 30 minutes, with stirring and whilst keeping the temperature at 70° C. When the addition has ended, the reaction medium is kept at 70° C. for 1 hour. 1 mol of powdered potassium hydroxide (70 g of 80% pure potassium hydroxide) and 1 mol of glycol bromohydrin (178 g) are then added. After heating for 1 hour, a further 1 mol of potassium hydroxide and 1 mol of glycol bromohydrin are added. The heating is continued for a further 1 hour and the cooled reaction medium is then poured into 7.5 liters of iced water. The expected product precipitates. It is filtered off and washed carefully with a 3N solution of sodium hydroxide and then with water. After drying in vacuo, it melts at 96° C.

Workup

  1. additionare then introduced in the course of 30 minutes
  2. customat 70° C
  3. additionWhen the addition
  4. temperatureAfter heating for 1 hour
  5. waitThe heating is continued for a further 1 hour
  6. customthe cooled reaction medium
  7. customThe expected product precipitates
  8. filtrationIt is filtered off
  9. washwashed carefully with a 3N solution of sodium hydroxide
  10. customAfter drying in vacuo, it melts at 96° C.

Sources & evidence

ORD record
ord-55f384cb505d4024aeca8449a6cf1e3c
Source dataset
uspto-grants-1991_06
Patent number
US05026401

Reaction notes

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